US5629264AExpiredUtilityPatentIndex 35
2-aryl-5,6-dihydropyrimidinones and herbicidal use thereof

Assignee: ROHM & HAASPriority: Mar 23, 1995Filed: Mar 23, 1995Granted: May 13, 1997
Est. expiryMar 23, 2015(expired)· nominal 20-yr term from priority
Inventors:TICE COLIN M BRYMAN LOIS M ROEMMELE RENEE C
C07D 239/22C07D 401/04A01N 43/54
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Claims
Abstract

A class of 2-aryl-5,6-dihydropyrimidinones and compositions thereof which are useful in the control of weeds is of the general formula <IMAGE> wherein Ar is a substituted or unsubstituted aryl or heteroaryl; R3 is an optionally substituted alkyl, alkenyl or alkynyl; R5a and R5b are each independently a hydrogen atom, halo, cyano or an optionally substituted alkyl, alkenyl, alkynyl, alkoxy or alkylthio; R6a and R6b are each independently a hydrogen atom, halo, cyano, an optionally substituted alkyl, alkenyl, alkynyl, alkoxy or alkylthioalkyl, cycloalkyl, optionally substituted aryl, aryloxy, heterocyclyl or aralkyl, alkylamino, dialkylamino or dialkylaminocarbonyl; R5a and R6a taken together with the carbon atoms to which they are attached may form a fused 4-7 member ring containing 2-5 methylenes; and X is an oxygen or a sulfur atom.
Claims

exact text as granted — not AI-modified
We claim: 
     
       1. A compound of the formula ##STR12## wherein Ar is a substituted or unsubstituted aryl or heteroaryl; R 3  is a haloalkyl, polyhaloalkyl, alkenyl, haloalkenyl, polyhaloalkenyl, alkynyl, haloalkynyl, polyhaloalkynyl, alkenynyl, alkoxyalkyl, haloalkoxyalkyl, oxoalkyl, trimethylsilylalkynyl or cyanoalkyl;   R 5a  and R 5b  are each independently a hydrogen atom, halo, alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkoxycarbonyl, alkoxycarbonylalkyl, haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy, polyhaloalkyl, polyhaloalkenyl, polyhaloalkynyl, polyhaloalkoxy, trimethylsilylalkynyl or cyano;   R 6a  and R 6b  are each independently a hydrogen atom, halo, alkyl, alkenyl, alkynyl, alkoxy, alkylthio, haloalkylthio, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, haloalkyl, haloalkoxy, haloalkenyl, haloalkynyl, polyhaloalkyl, polyhaloalkoxy, polyhaloalkylthio, polyhaloalkenyl, polyhaloalkynyl, cycloalkyl, aryl, aryloxy, heterocyclyl, aralkyl, alkylamino, dialkylamino, dialkylaminocarbonyl, or cyano;   R 5a  and R 6a  taken together with the carbon atoms to which they are attached may form a fused 4-7 member ring containing 2-5 methylenes; and   X is an oxygen or a sulfur atom.   
     
     
       2. The compound of claim 1 wherein Ar is furyl, phenyl, naphthyl, pyridyl or thienyl, or furyl, phenyl, naphthyl, pyridyl or thienyl substituted with up to three substituents independently selected from bromo, chloro, fluoro, (C 1  -C 12 )alkyl, cyclo(C 3  -C 8 )alkyl, (C 2  -C 12 )alkenyl, cyclo(C 3  -C 8 )alkenyl, (C 2  -C 12 )alkynyl, halo(C 1  -C 12 )alkyl, polyhalo(C 1  -C 12 )alkyl, halo(C 2  -C 12 )alkenyl, polyhalo(C 2  -C 12 )alkenyl, halo(C 2  -C 6 )alkynyl, polyhalo(C 2  -C 6 )alkynyl, (C 1  -C 12 )alkoxy, (C 1  -C 12 )alkylthio, (C 1  -C 12 )alkylsulfonyl, (C 1  -C 12 )alkylsulfinyl, phenyl, phen(C 1  -C 12 )alkyl, phen(C 2  -C 12 )alkenyl, phen(C 2  -C 12 )alkynyl, cyano, halo(C 1  -C 12 )alkoxy, 1,3-dioxalan-2-yl, hydroxyimino, polyhalo(C 1  -C 12 )alkoxy and nitro;   R 3  is halo(C 1  -C 3 )alkyl, polyhalo(C 1  -C 3 )alkyl, (C 3  -C 4 )alkenyl, halo(C 3  -C 4 )alkenyl, polyhalo(C 3  -C 4 )alkenyl, (C 3  -C 6 )alkynyl, halo(C 3  -C 6 )alkynyl, polyhalo(C 3  -C 6 )alkynyl, (C 5  -C 6 )alkenynyl, (C 1  -C 6 )alkoxy(C 1  -C 6 )alkyl, halo(C 1  -C 6 )alkoxy(C 1  -C 6 )alkyl, 2-oxo(C 2  -C 3 )alkyl, trimethylsilyl(C 3  -C 4 )alkynyl or cyano(C 1  -C 6 )alkyl;   R 5a  and R 5b  are each independently a hydrogen atom, (C 1  -C 6 )alkyl, (C 2  -C 6 )alkenyl, (C 2  -C 6 )alkynyl, trimethylsilyl(C 2  -C 3 )alkynyl, (C 1  -C 6 )alkoxy, halo(C 1  -C 6 )alkyl, polyhalo(C 1  -C 6 )alkyl, halo(C 2  -C 6 )alkenyl, polyhalo(C 2  -C 6 )alkenyl, halo(C 2  -C 6 )alkynyl, polyhalo(C 2  -C 6 )alkynyl, halo(C 1  -C 6 )alkoxy, polyhalo(C 1  -C 6 )alkoxy, (C 1  -C 6 )alkoxycarbonyl, (C 1  -C 3 )alkoxycarbonyl(C 1  -C 3 )alkyl, (C 1  -C 6 )alkylthio, halo or cyano;   R 6a  and R 6b  are each independently a hydrogen atom, halo, (C 1  -C 3 )alkyl, (C 2  -C 6 )alkenyl, (C 2  -C 6 )alkynyl, halo(C 1  -C 6 )alkyl or polyhalo(C 1  -C 6 )alkyl, halo(C 2  -C 6 )alkenyl or polyhalo(C 2  -C 6 )alkenyl, halo(C 2  -C 6 )alkynyl or polyhalo(C 2  -C 6 )alkynyl, (C 1  -C 6 )alkoxy(C 1  -C 4 )alkyl, (C 1  -C 6 )alkoxy, (C 1  -C 6 )alkylthio, C 1  -C 3 )alkoxycarbonyl, (C 1  -C 3 )alkoxycarbonyl(C 1  -C 3 )alkyl, cyclo(C 3  -C 7 )alkyl, halo(C 1  -C 6 )alkylthio, polyhalo(C 1  -C 6 )alkythio, halo(C 1  -C 6 )alkoxy, polyhalo(C 1  -C 6 )alkoxy, (C 4  -C 5 )heterocyclyl, (C 1  -C 3 )alkylamino, di(C 1  -C 3 )alkylamino, di(C 1  -C 3 )alkylaminocarbonyl, cyano, aryl, aryloxy, ar(C 1  -C 4 )alkyl, or aryl, aryloxy or ar(C 1  -C 4 )alkyl substituted on the aryl ring with up to three substituents independently selected from the group consisting of halo, (C 1  -C 6 )alkyl, cyclo(C 5  -C 6 )alkyl, (C 2  -C 6 )alkenyl, cyclo(C 3  -C 8 )alkenyl, (C 2  -C 6 )alkynyl, halo(C 1  -C 6 )alkyl, polyhalo(C 1  -C 6 )alkyl, halo(C 2  -C 6 )alkenyl, polyhalo(C 2  -C 6 )alkenyl, halo(C 2  -C 6 )alkynyl, polyhalo(C 2  -C 6 )alkynyl, (C 1  -C 6 )alkoxy, (C 1  -C 6 )alkylthio, C 1  -C 6 )alkylsulfonyl, (C 1  -C 6 )alkylsulfinyl, phenyl, phen(C 1  -C 6 )alkyl, phen(C 2  -C 6 )alkenyl, phen(C 2  -C 6 )alkynyl, cyano, halo(C 1  -C 6 )alkoxy, 1,3-dioxalan-2-yl, hydroxyimino and nitro; and   X is an oxygen atom.   
     
     
       3. The compound of claim 2 wherein Ar is phenyl, 3-methylphenyl, 3methoxyphenyl, 3-nitrophenyl, 4-fluorophenyl, 4-chlorophenyl, 3-trifluoromethylphenyl, 3-bromophenyl, 3-chlorophenyl, 3-fluorophenyl, 3-trifluoromethoxyphenyl, 3-cyanophenyl, 3-(1,3-dioxolan-2-yl)phenyl, 3-(hydroxyimino)phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethoxyphenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3-chloro-4-fluorophenyl, 3,4-difluorophenyl, 3-fluoro-5-trifluoromethylphenyl, and 3,4,5-trifluorophenyl, 6-chloro-2-pyridyl, 3-pyridyl, 5-bromo-3-pyridyl, 5,6-dichloro-3-pyridyl, 5-chloro-3-pyridyl, 4-pyridyl, 2-fluoro-4-pyridyl, 2-chloro-4-pyridyl, 2-chloro-6-methyl-4-pyridyl, 2-methyl-4-pyridyl, 2-methoxy-4-pyridyl, 2-cyano-4-pyridyl, 2,6-difluoro-4-pyridyl, 2,6-dichloro-4-pyridyl, 2-furyl, 3-furyl, 2-naphthyl, 2-thienyl, 3-thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl or 2,5-dichloro-3-thienyl. 
     
     
       4. The compound of claim 3 wherein Ar is phenyl, 3-fluorophenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 3-chlorophenyl, 2-chloro-4-pyridyl, 2-fluoro-4pyridyl, 5-chloro-3-pyridyl, 2,6-dichloro-4-pyridyl or 5-chloro-3-thienyl. 
     
     
       5. The compound of claim 2 wherein R 3  is allyl, 3-chloroallyl, pentynyl, propargyl, 2-butynyl, iodopropargyl, bromopropargyl, methoxymethyl, 2-methoxyethyl, acetonyl, 3-(trimethylsilyl)propargyl, pent-4-en-2-ynyl or cyanomethyl. 
     
     
       6. The compound of claim 5 wherein R 3  is 2-pentynyl, propargyl, 2-butynyl, iodopropargyl or methoxymethyl. 
     
     
       7. The compound of claim 2 wherein R 5a  and R 5b  are each independently a hydrogen atom, methyl, ethyl, n-propyl, isopropyl, propargyl, methoxy, methylthio, methoxycarbonylmethyl, allyl, fluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, chloro and fluoro. 
     
     
       8. The compound of claim 7 wherein R 5a  and R 5b  are each independently a hydrogen atom, methyl, ethyl, methoxycarbonyl, ethoxycarbonyl, allyl or propargyl. 
     
     
       9. The compound of claim 2 wherein R 6a  and R 6b  are each independently a hydrogen atom, phenyl, phenyl substituted with up to two substituents independently selected from halo, methyl, ethyl and trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-methyl-l-propenyl, allyl, 3-thienyl, 3-furyl, 2-thienyl, 4-pyridyl, methoxy, ethoxy, ethoxycarbonyl, but-2-ynyl, but-3-ynyl, propargyl, fluoro, bromo, chloro, trifluoromethyl, pentafluoroethyl, trichloromethyl, bromomethyl, chloromethyl, difluoromethyl, chlorodifluoromethyl, difluoromethoxy, trifluoromethoxy, methylthio, methoxymethyl, benzyl, cyclopropyl, cyclobutyl, cyclopentyl, dimethylamino or dimethylaminocarbonyl. 
     
     
       10. The compound of claim 9 wherein R 6a  and R 6b  are each independently a hydrogen atom, phenyl, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, allyl or propargyl. 
     
     
       11. A herbicidal composition comprising a compound of the formula ##STR13## wherein Ar is a substituted or unsubstituted aryl or heteroaryl; R 3  is an alkyl, haloalkyl, polyhaloalkyl, alkenyl, haloalkenyl, polyhaloalkenyl, alkynyl, haloalkynyl, polyhaloalkynyl, alkenynyl, alkoxyalkyl, dialkoxyalkyl, haloalkoxyalkyl, oxoalkyl, trimethylsilylalkynyl or cyanoalkyl;   R 5a  and R 5b  are each independently a hydrogen atom, halo, alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkoxycarbonyl, alkoxycarbonylalkyl, haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy, polyhaloalkyl, polyhaloalkenyl, polyhaloalkynyl, polyhaloalkoxy, trimethylsilylalkynyl or cyano;   R 6a  and R 6b  are each independently a hydrogen atom, halo, alkyl, alkenyl, alkynyl, alkoxy, alkylthio, haloalkylthio, alkoxyalkyl, alkoxycarbonyl, alkoxycarbonylalkyl, haloalkyl, haloalkoxy, haloalkenyl, haloalkynyl, polyhaloalkyl, polyhaloalkoxy, polyhaloalkylthio, polyhaloalkenyl, polyhaloalkynyl, cycloalkyl, aryl, aryloxy, heterocyclyl, aralkyl, alkylamino, dialkylamino, dialkylaminocarbonyl, or cyano;   R 5a  and R 6a  taken together with the carbon atoms to which they are attached may form a fused 4-7 member ring containing 2-5 methylenes;   X is an oxygen or a sulfur atom; and   an agronomically acceptable carrier.   
     
     
       12. The composition of claim 11 wherein Ar is furyl, phenyl, naphthyl, pyridyl or thienyl, or furyl, phenyl, naphthyl, pyridyl or thienyl substituted with up to three substituents independently selected from bromo, chloro, fluoro, (C 1  -C 12 )alkyl, cyclo(C 3  -C 8 )alkyl, (C 2  -C 12 )alkenyl, cyclo(C 3  -C 8 )alkenyl, (C 2  -C 12 )alkynyl, halo(C 1  -C 12 )alkyl, polyhalo(C 1  -C 12 )alkyl, halo(C 2  -C 12 )alkenyl, polyhalo(C 2  -C 12 )alkenyl, halo(C 2  -C 6 )alkynyl, polyhalo(C 2  -C 6 )alkynyl, (C 1  -C 12 )alkoxy, (C 1  -C 12 )alkylthio, (C 1  -C 12 )alkylsulfonyl, (C 1  -C 12 )alkylsulfinyl, phenyl, phen(C 1  -C 12 )alkyl, phen(C 2  -C 12 )alkenyl, phen(C 2  -C 12 )alkynyl, cyano, halo(C 1  -C 12 )alkoxy, 1,3-dioxalan-2-yl, hydroxyimino, polyhalo(C 1  -C 12 )alkoxy and nitro;   R 3  is (C 1  -C 3 )alkyl, halo(C 1  -C 3 )alkyl, polyhalo(C 1  -C 3 )alkyl, (C 3  -C 4 )alkenyl, halo(C 3  -C 4 )alkenyl, polyhalo(C 3  -C 4 )alkenyl, (C 3  -C 6 )alkynyl, halo(C 3  -C 6 )alkynyl, polyhalo(C 3  -C 6 )alkynyl, (C 5  -C 6 )alkenynyl, (C 1  -C 6 )alkoxy(C 1  -C 6 )alkyl, di(C 1  -C 6 )alkoxy(C 1  -C 6 )alkyl, halo(C 1  C 6 )alkoxy(C 1  -C 6 )alkyl, 2-oxo(C 2  -C 3 )alkyl, trimethylsilyl(C 3  -C 4 )alkynyl or cyano(C 1  -C 6 )alkyl;   R 5a  and R 5b  are each independently a hydrogen atom, (C 1  -C 6 )alkyl, (C 2  C 6 )alkenyl, (C 2  -C 6 )alkynyl, trimethylsilyl(C 2  -C 3 )alkynyl, (C 1  -C 6 )alkoxy, halo(C 1  -C 6 )alkyl, polyhalo(C 1  -C 6 )alkyl, halo(C 2  -C 6 )alkenyl, polyhalo(C 2  -C 6 )alkenyl, halo(C 2  -C 6 )alkynyl, polyhalo(C 2  -C 6 )alkynyl, halo(C 1  -C 6 )alkoxy, polyhalo(C 1  -C 6 )alkoxy, (C 1  -C 6 )alkoxycarbonyl, (C 1  -C 3 )alkoxycarbonyl(C 1  -C 3 )alkyl, C 1  -C 6 )alkylthio, halo or cyano;   R 6a  and R 6b  are each independently a hydrogen atom, halo, (C 1  -C 8 )alkyl, (C 2  -C 6 )alkenyl, (C 2  -C 6 )alkynyl, halo(C 1  -C 6 )alkyl or polyhalo(C 1  -C 6 )alkyl, halo(C 2  -C 6 )alkenyl or polyhalo(C 2  -C 6 )alkenyl, halo(C 2  -C 6 )alkynyl or polyhalo(C 2  C 6 )alkynyl, (C 1  -C 6 )alkoxy(C 1  -C 4 )alkyl, (C 1  -C 6 )alkoxy, (C 1  -C 6 )alkylthio, C 1  -C 3 )alkoxycarbonyl, (C 1  -C 3 )alkoxycarbonyl(C 1  -C 3 )alkyl, cyclo(C 3  -C 7 )alkyl, halo(C 1  -C 6 )alkylthio, polyhalo(C 1  -C 6 )alkythio, halo(C 1  -C 6 )alkoxy, polyhalo(C 1  -C 6 )alkoxy, (C 4  -C 5 )heterocyclyl, (C 1  -C 3 )alkylamino, di(C 1  -C 3 )alkylamino, di(C 1  -C 3 )alkylaminocarbonyl, cyano, aryl, aryloxy, ar(C 1  -C 4 )alkyl, or aryl, aryloxy or ar(C 1  -C 4 )alkyl substituted on the aryl ring with up to three substituents independently selected from the group consisting of halo, (C 1  -C 6 )alkyl, cyclo(C 5  -C 6 )alkyl, (C 2  -C 6 )alkenyl, cyclo(C 3  -C 8 )alkenyl, (C 2  -C 6 )alkynyl, halo(C 1  -C 6 )alkyl, polyhalo(C 1  -C 6 )alkyl, halo(C 2  -C 6 )alkenyl, polyhalo(C 2  -C 6 )alkenyl, halo(C 2  C 6 )alkynyl, polyhalo(C 2  -C 6 )alkynyl, (C 1  -C 6 )alkoxy, (C 1  -C 6 )alkylthio, (C 1  -C 6 )alkylsulfonyl, (C 1  -C 6 )alkylsulfinyl, phenyl, phen(C 1  -C 6 )alkyl, phen(C 2  C 6 )alkenyl, phen(C 2  -C 6 )alkynyl, cyano, halo(C 1  -C 6 )alkoxy, 1,3-dioxalan-2-yl, hydroxyimino and nitro; and   X is an oxygen atom.   
     
     
       13. The composition of claim 12 wherein Ar is phenyl, 3-methylphenyl, 3-methoxyphenyl, 3-nitrophenyl, 4-fluorophenyl, 4-chlorophenyl, 3-trifluoromethylphenyl, 3-bromophenyl, 3-chlorophenyl, 3-fluorophenyl, 3-trifluoromethoxyphenyl, 3-cyanophenyl, 3-(1,3-dioxolan-2-yl)phenyl, 3-(hydroxyimino)phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-trifluoromethoxyphenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 3-chloro-4-fluorophenyl, 3,4-difluorophenyl, 3-fluoro-5-trifluoromethylphenyl, and 3,4,5-trifluorophenyl 6-chloro-2-pyridyl, 3-pyridyl, 5-bromo-3-pyridyl, 5,6-dichloro-3-pyridyl, 5-chloro-3-pyridyl, 4-pyridyl, 2-fluoro-4-pyridyl, 2-chloro-4-pyridyl, 2-chloro-6-methyl-4-pyridyl, 2-methyl-4-pyridyl, 2-methoxy-4-pyridyl, 2-cyano-4-pyridyl, 2,6-difluoro-4-pyridyl, 2,6-dichloro-4-pyridyl, 2-furyl. 3-furyl, 2-naphthyl, 2-thienyl, 3-thienyl, 4-chloro-2-thienyl, 5-chloro-2-thienyl, 5-chloro-3-thienyl or 2,5-dichloro-3-thienyl. 
     
     
       14. The composition of claim 13 wherein Ar is phenyl, 3-fluorophenyl, 3,5-difluorophenyl, 3,5-dichlorophenyl, 3-chlorophenyl, 2-chloro-4-pyridyl, 2-fluoro-4-pyridyl, 5-chloro-3-pyridyl, 2,6-dichloro-4-pyridyl or 5-chloro-3-thienyl. 
     
     
       15. The composition of claim 12 wherein R 3  is ethyl, allyl, 3-chloroallyl, pentynyl, propargyl, 2-butynyl, iodopropargyl, bromopropargyl, methoxymethyl, 2-methoxyethyl, 2,2-dimethoxypropyl, acetonyl, 3-(trimethylsilyl)propargyl, pent-4-en-2-ynyl or cyanomethyl. 
     
     
       16. The composition of claim 15 wherein R 3  is 2-pentynyl, propargyl, 2-butynyl, iodopropargyl or methoxymethyl. 
     
     
       17. The composition of claim 12 wherein R 5a  and R 5b  are each independently a hydrogen atom, methyl, ethyl, n-propyl, isopropyl, propargyl, methoxy, methylthio, methoxycarbonylmethyl, allyl, fluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, chloro and fluoro. 
     
     
       18. The composition of claim 17 wherein R 5a  and R 5b  are each independently a hydrogen atom, methyl, ethyl, methoxycarbonyl, ethoxycarbonyl, allyl or propargyl. 
     
     
       19. The composition of claim 12 wherein R 6a  and R 6b  are each independently a hydrogen atom, phenyl, phenyl substituted with up to two substituents independently selected from halo, methyl, ethyl and trifluoromethyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-methyl-l-propenyl, allyl, 3-thienyl, 3-furyl, 2-thienyl, 4-pyridyl, methoxy, ethoxy, ethoxycarbonyl, but-2-ynyl, but-3-ynyl, propargyl, fluoro, bromo, chloro, trifluoromethyl, pentafluoroethyl, trichloromethyl, bromomethyl, chloromethyl, difluoromethyl, chlorodifluoromethyl, difluoromethoxy, trifluoromethoxy, methylthio, methoxymethyl, benzyl, cyclopropyl, cyclobutyl, cyclopentyl, dimethylamino or dimethylaminocarbonyl. 
     
     
       20. The composition of claim 19 wherein R 6a  and R 6b  are each independently a hydrogen atom, phenyl, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, allyl or propargyl. 
     
     
       21. A method of controlling a weed comprising applying a herbicidally effective amount of a composition of claims 11 or 12 to the weed, to the locus of the weed or to the growth medium of the weed. 
     
     
       22. The compound of claims 1 or 2 which is 2-(3-chlorophenyl)-3-propargyl-6-trifluoromethyl-5,6-dihydropyrimidin-4-one, 2-(3,5-dichlorophenyl)-3-propargyl-6-trifluoromethyl-5,6-dihydropyrimidin-4-one or 5-ethyl-2-phenyl-3-propargyl-6-trifluoromethyl-5,6-dihydropyrimidin-4-one.
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